1,2,4-Triazolylsodium → tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-{2-[2-(2-[1,2,4]triazol-1-ylethyl)phenoxy]ethoxy}piperidine-1-carboxylate

HRID 1176254Notes

Reaction equation

HRID 1176254 reaction equation
[NH:1]1[CH:5]=[N:4][C-:3]=[N:2]1.[Na+].[CH3:7][O:8][C:9]1[CH:62]=[CH:61][CH:60]=[CH:59][C:10]=1[CH2:11][O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH:24]2[O:36][CH2:37][CH2:38][O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH2:46][CH2:47]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:19][CH:18]=1>CN(C)C=O.COC(C)(C)C>[CH3:7][O:8][C:9]1[CH:62]=[CH:61][CH:60]=[CH:59][C:10]=1[CH2:11][O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[CH2:25][CH:24]2[O:36][CH2:37][CH2:38][O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH2:46][CH2:47][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 547199651,2,4-TriazolylsodiumHCID 86609986Tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(2-{2-[2-(toluene-4-sulphonyloxy)ethyl]phenoxy}-ethoxy)piperidine-1-carboxylate

Product 1

HCID 68497847tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-{2-[2-(2-[1,2,4]triazol-1-ylethyl)phenoxy]ethoxy}piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
90 °C

Procedure

0.051 g of sodium 1,2,4-triazolide is admixed with a solution of 0.10 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(2-{2-[2-(toluene-4-sulphonyloxy)ethyl]phenoxy}-ethoxy)piperidine-1-carboxylate in 3 ml of N,N-dimethylformamide. The reaction mixture is stirred at 90° C. over 40 minutes. The mixture is cooled to room temperature, diluted with tert-butyl methyl ether and washed with water. The water phase is extracted with tert-butyl methyl ether. The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.13 (2:1 EtOAc-heptane); Rt=5.66.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. washwashed with water
  3. extractionThe water phase is extracted with tert-butyl methyl ether
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-70726b33ff5a4d96a19235e5866f8b0d
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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